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PYRETHRIN I
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Name

PYRETHRIN I

 EINECS N/A
CAS No. 121-21-1 Density 1.04g/cm3
PSA 43.37000 LogP 4.55820
Solubility N/A Melting Point N/A
Formula C21H28 O3 Boiling Point 424.3°Cat760mmHg
Molecular Weight 328.452 Flash Point 182.3°C
Transport Information N/A Appearance N/A
Safety Poison by ingestion and intravenous routes. When heated to decomposition it emits acrid smoke and irritating fumes. An insecticide. See also PYRETHRIN; PYRETHRIN II; PYRETHRINS. Risk Codes 20/21/22-50/53
Molecular Structure Molecular Structure of 121-21-1 (PYRETHRIN 1) Hazard Symbols
Synonyms

Cyclopropanecarboxylicacid, 2,2-dimethyl-3-(2-methyl-1-propenyl)-,(1S)-2-methyl-4-oxo-3-(2Z)-2,4-pentadienyl-2-cyclopenten-1-yl ester, (1R,3R)-(9CI); Cyclopropanecarboxylic acid, 2,2-dimethyl-3-(2-methyl-1-propenyl)-,2-methyl-4-oxo-3-(2,4-pentadienyl)-2-cyclopenten-1-yl ester, [1R-[1a[S*(Z)],3b]]-; Cyclopropanecarboxylic acid,2,2-dimethyl-3-(2-methylpropenyl)-, ester with4-hydroxy-3-methyl-2-(2,4-pentadienyl)-2-cyclopenten-1-one (8CI); Pyrethrin 1(6CI); (+)-Pyrethronyl (+)-trans-chrysanthemate; Chrysanthemummonocarboxylicacid pyrethrolone ester; Pyrethrin I

Article Data 8

PYRETHRIN I Synthetic route

4638-92-0

(1R,3R)-trans-chrysanthemic acid

487-67-2

(S)-(+)-pyrethrolone

121-21-1

pyrethrin I

Conditions
ConditionsYield
Stage #1: (1R,3R)-trans-chrysanthemic acid With 1-methyl-1H-imidazole; p-toluenesulfonyl chloride In acetonitrile at 0 - 5℃; for 0.5h; Inert atmosphere;
Stage #2: (S)-(+)-pyrethrolone In acetonitrile at 20 - 25℃; for 2h; Inert atmosphere;		74%
acyl chloride of (1R)-2.2-dimethyl-3t-<2-methyl-propenyl>-cyclopropane-carboxylic acid-(1r)

acyl chloride of (1R)-2.2-dimethyl-3t-<2-methyl-propenyl>-cyclopropane-carboxylic acid-(1r)

(S)-5-hydroxy-1-methyl-2-c.4)-yl>-cyclopenten-(1)-one-(3)

(S)-5-hydroxy-1-methyl-2-c.4)-yl>-cyclopenten-(1)-one-(3)

121-21-1

pyrethrin I

Conditions
ConditionsYield
With pyridine; benzene

chrysanthemoyl CoA

487-67-2

(S)-(+)-pyrethrolone

121-21-1

pyrethrin I

Conditions
ConditionsYield
With (maltose-binding protein)-fusedTanacetum cinerariifolium GDSL lipase/esterase,recombinant, molecular weight: 81689 Da In aq. buffer at 25℃; for 0.166667h; pH=7.5; Kinetics; Reagent/catalyst; Enzymatic reaction;
4638-92-0

(1R,3R)-trans-chrysanthemic acid

121-21-1

pyrethrin I

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: thionyl chloride / 0.5 h / 50 - 100 °C
2: 1 h / 0 °C / Reflux
3: 1,8-diazabicyclo[5.4.0]undec-7-ene / tetrahydrofuran / 0 °C
View Scheme
4489-14-9

(1R)-trans-3-(2-methyl-1-propenyl)-2,2-dimethylcyclopropanecarboxylic acid chloride

C11H15IO2

121-21-1

pyrethrin I

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 1 h / 0 °C / Reflux
2: 1,8-diazabicyclo[5.4.0]undec-7-ene / tetrahydrofuran / 0 °C
View Scheme

C21H29IO3

121-21-1

pyrethrin I

Conditions
ConditionsYield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In tetrahydrofuran at 0℃;
22373-75-7

(S)-4-hydroxy-3-methyl-2-(2-propenyl)-2-cyclopenten-1-one

121-21-1

pyrethrin I

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: [2-(1-methylethoxy-O)phenylmethyl-C](nitrato-O,O'){rel-(2R,5R,7R)-adamantane-2,1-diyl[3-(2,4,6-trimethylphenyl)-1-imidazolidinyl-2-ylidene]}ruthenium / tetrahydrofuran / 12 h / 35 °C
2: 1 h / 0 °C / Reflux
3: 1,8-diazabicyclo[5.4.0]undec-7-ene / tetrahydrofuran / 0 °C
View Scheme

(S)-(+)-4-hydroxy-3-methyl-2-(pent-4-en-2-ynyl)-2-cyclopenten-1-one

121-21-1

pyrethrin I

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: hydrogenchloride; zinc / ethanol; water / 16 h / 75 - 80 °C / Inert atmosphere
2.1: 1-methyl-1H-imidazole; p-toluenesulfonyl chloride / acetonitrile / 0.5 h / 0 - 5 °C / Inert atmosphere
2.2: 2 h / 20 - 25 °C / Inert atmosphere
View Scheme
97-41-6, 1802-02-4, 7377-84-6, 15543-65-4, 16642-27-6, 34909-55-2, 41641-25-2, 41641-26-3, 41641-27-4

ethyl trans-(+/-)-chrysanthemate

121-21-1

pyrethrin I

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: potassium hydroxide / ethanol; water / 3 h
2.1: (S)-1-(1-Naphthyl)ethylamine / ethanol / 3 h / 20 °C
3.1: 1-methyl-1H-imidazole; p-toluenesulfonyl chloride / acetonitrile / 0.5 h / 0 - 5 °C / Inert atmosphere
3.2: 2 h / 20 - 25 °C / Inert atmosphere
View Scheme
827-90-7, 2259-14-5, 2935-23-1, 4638-92-0, 10453-89-1, 15259-78-6, 26771-06-2, 26771-11-9, 705-16-8

trans-chrysanthemic acid

121-21-1

pyrethrin I

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: (S)-1-(1-Naphthyl)ethylamine / ethanol / 3 h / 20 °C
2.1: 1-methyl-1H-imidazole; p-toluenesulfonyl chloride / acetonitrile / 0.5 h / 0 - 5 °C / Inert atmosphere
2.2: 2 h / 20 - 25 °C / Inert atmosphere
View Scheme

PYRETHRIN I Chemical Properties

Molecular Formula: C21H28O3
Molecular Weight: 328.49
EINECS: 204-455-8
Density: 1.04g/cm3
Flash Point: 182.3°C
Storage temp: 0-6°C
Enthalpy of Vaporization: 67.88 kJ/mol 
Boiling Point: 424.3 °C at 760 mmHg 
Vapour Pressure: 2.09E-07 mmHg at 25°C 
Boiling Point of Pyrethrony l (121-21-1): 424.3°Cat760mmHg
IUPAC Name: [(1S)-2-methyl-4-oxo-3-[(2E)-penta-2,4-dienyl]cyclopent-
2-en-1-yl] (1R,3R)-2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropane-
1-carboxylate
Synonyms: Pyrethrony l ; (+)-Pyrethronyl(+)-trans-chrysanthemate ; 2,2-Dimethyl-3-(2-methyl-1-propenyl)cyclopropanecarboxylicacid2-methyl-4-oxo ; 2,2-Dimethyl-3-(2-methylpropenyl)-cyclopropaneacrylicaciesterwith4-hydr ; 2,2-Dimethyl-3-(2-methylpropenyl)-cyclopropanecarboxylicaciesterwith4-h
Following is the molecular structure of Pyrethrony l (121-21-1):

PYRETHRIN I Toxicity Data With Reference

1.    

orl-rat LD50:260 mg/kg

     PCBPBS    Pesticide Biochemistry and Physiology. 2 (1972),308.
2.    

ivn-rat LDLo:5 mg/kg

     BIOGAL    Biologico. 41 (10)(1975),283.

PYRETHRIN I Safety Profile

Poison by ingestion and intravenous routes. When heated to decomposition it emits acrid smoke and irritating fumes. An insecticide.
Safety Information of Pyrethrony l (121-21-1):
Hazard Codes: Xn,N
Xn: Harmful N:Dangerous for the environment
Risk Statements: 20/21/22-50/53
20/21/22: Harmful by inhalation, in contact with skin and if swallowed 
50/53: Very Toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment  
Safety Statements: 13-60-61
13: Keep away from food, drink and animal feeding stuffs 
60: This material and/or its container must be disposed of as hazardous waste 
61: Avoid release to the environment. Refer to special instructions safety data sheet  
RIDADR  2902
HazardClass: 6.1(b)
PackingGroup: III
 

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